tert-butyl 3-(3-methoxy-4-nitro-1H-pyrazol-1-yl)azetidine-1-carboxylate → tert-butyl 3-(4-amino-3-methoxy-1H-pyrazol-1-yl)azetidine-1-carboxylate

Participants

Reaction Steps

A nitrogen-flushed round bottom flask was charged with tert-butyl 3-(3-methoxy-4-nitro-1H-pyrazol-1-yl)azetidine-1-carboxylate (188 mg, 0.63 mmol, 1.00 eq), 10% Pd/C (100 mg) and methanol (10 mL). The reaction mixture was sparged with hydrogen for 5 min then stirred vigorously under hydrogen atmosphere for 18 hr. The reaction mixture was then sparged with nitrogen, filtered through Celite®, concentrated, and azeotroped from toluene (2×20 mL) to give an oil that was used without further purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.04 (s, 1H), 4.82 (tt, J=5.4, 7.9 Hz, 1H), 4.15 (t, J=8.3 Hz, 2H), 4.04-3.95 (m, 2H), 3.79 (s, 3H), 3.44 (br. s., 2H), 1.40 (s, 9H). m/z (APCI+) for C7H13N4O 169.2 (M−Boc+H)+.

Provenance & Evidence